CN104955928B - Pyrans dispersant - Google Patents
Pyrans dispersant Download PDFInfo
- Publication number
- CN104955928B CN104955928B CN201380071774.7A CN201380071774A CN104955928B CN 104955928 B CN104955928 B CN 104955928B CN 201380071774 A CN201380071774 A CN 201380071774A CN 104955928 B CN104955928 B CN 104955928B
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- Prior art keywords
- compound
- dispersant
- weight
- aldehyde
- polyolefin
- Prior art date
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 76
- 150000004880 oxines Chemical class 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims description 53
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 32
- 150000001299 aldehydes Chemical class 0.000 claims description 31
- -1 Hydrogen pyrans Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229920000098 polyolefin Polymers 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 26
- 239000007795 chemical reaction product Substances 0.000 claims description 24
- 239000000314 lubricant Substances 0.000 claims description 19
- 238000006467 substitution reaction Methods 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
- 238000006596 Alder-ene reaction Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000012805 post-processing Methods 0.000 claims description 4
- 239000011149 active material Substances 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000010478 Prins reaction Methods 0.000 claims description 2
- 238000007171 acid catalysis Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000010705 motor oil Substances 0.000 abstract description 11
- 238000007789 sealing Methods 0.000 abstract description 11
- 238000005260 corrosion Methods 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 4
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229920002367 Polyisobutene Polymers 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 24
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- 150000001721 carbon Chemical group 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
- 238000002485 combustion reaction Methods 0.000 description 13
- 239000003599 detergent Substances 0.000 description 13
- 230000001050 lubricating effect Effects 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229920000768 polyamine Polymers 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 229930195733 hydrocarbon Chemical group 0.000 description 10
- 229960002317 succinimide Drugs 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000004215 Carbon black (E152) Chemical group 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 150000004292 cyclic ethers Chemical class 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 7
- 125000001033 ether group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 229940121354 immunomodulator Drugs 0.000 description 3
- 230000002584 immunomodulator Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical compound CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LYJZNXAVZMEXDH-UHFFFAOYSA-N octadecan-8-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCC(OC(=O)C(C)=C)CCCCCCC LYJZNXAVZMEXDH-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 1
- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YAWNFGAHEUCLNJ-UHFFFAOYSA-N [B].OB(O)O Chemical compound [B].OB(O)O YAWNFGAHEUCLNJ-UHFFFAOYSA-N 0.000 description 1
- PRPAGESBURMWTI-UHFFFAOYSA-N [C].[F] Chemical compound [C].[F] PRPAGESBURMWTI-UHFFFAOYSA-N 0.000 description 1
- PMUIBVMKQVKHBE-UHFFFAOYSA-N [S].NC(N)=O Chemical group [S].NC(N)=O PMUIBVMKQVKHBE-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
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- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
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- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 1
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- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
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- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M157/00—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential
- C10M157/04—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, each of these compounds being essential at least one of them being a nitrogen-containing compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/18—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member containing only hydrogen and carbon atoms in addition to the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
- C08F110/10—Isobutene
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
-
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/08—Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/36—Seal compatibility, e.g. with rubber
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/43—Sulfur free or low sulfur content compositions
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/45—Ash-less or low ash content
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
Abstract
Disclosed technology, which is related to, to be shown neutral pH and there is enough polarity to serve as the ashless compound of dispersant.Disclosed technology further relates to ashless compound prevents engine deposits without making sealing degrade or improve the purposes of (contributing to) corrosion in engine lubricant as dispersant.
Description
Background of invention
Disclosed technology is related to enough polarity to serve as the ashless compound of the non-alkaline of dispersant.Disclosed
Technology further relates to ashless compound and is used as dispersant to prevent engine deposits without dropping sealing in engine lubricant
Solution or the purposes for improving the corrosion of (contributing to) yellow metal.
Depending on the construction of compound, detersive or compound dispersing agent can obtain non-volatile materials, example in burning
Such as boron oxide or phosphorus pentoxide.However, ashless detergent and dispersant do not include metal generally, therefore will not be obtained in burning
To containing calx.The ashless dispersant of many types is as known in the art.
(1) " carboxylic dispersants " are carboxylic acid acylating agent's (acid, acid anhydride, ester etc.) and nitrogen-containing compound (such as amine), organic hydroxylic
Compound (such as aliphatic compounds, including unitary and polyalcohol, or aromatic compounds, including phenol and naphthols and aromatics
Amine) and/or alkaline inorganic material reaction reaction product.These reaction products include acid imide, the acid amides of carboxylic ester dispersants
With ester reaction product.The example of these " carboxylic dispersants " is described in BP 1,306,529 and many United States Patent (USP)s, bag
Include following：3,219,666、3,316,177、3,340,281、3,351,552、3,381,022、3,433,744、3,444,170、
3,467,668th, 3,501,405,3,542,680,3,576,743,3,632,511,4,234,435 and Re.26,433.
(2) " amine dispersant " is the reaction product of higher molecular weight aliphatic halide and amine, preferably polyalkylene polyamine.Its
Example is described in for example following United States Patent (USP)：3,275,554th, 3,438,757,3,454,555 and 3,565,804.
(3) " Mannich dispersant " is alkylphenol and aldehyde (especially formaldehyde) and amine (especially polyalkylene polyamine)
Reaction product.Material is illustrative described in following United States Patent (USP)：3,036,003、3,236,770、3,414,347、3,
448,047、3,461,172、3,539,633、3,586,629、3,591,598、3,634,515、3,725,480、3,726,882
With 3,980,569.
(4) dispersant is post-processed by making carboxylic acid, amine or Mannich dispersant and reagent such as dimercaptothiodiazole, urea, sulphur
Urea, carbon disulfide, aldehyde, ketone, carboxylic acid, hydrocarbon substituted succinyl oxide, nitrile, epoxides, boron compound, phosphorus compound etc. react and obtained
Arrive.This kind of examples material is described in following United States Patent (USP)：3,200,107、3,282,955、3,367,943、3,513,093、
3,639,242nd, 3,649,659,3,442,808,3,455,832,3,579,450,3,600,372,3,702,757 and 3,708,
422。
(5) polymeric dispersant is oil-soluble monomer such as decyl-octyl methacrylate, vinyl decyl ether and high molecular weight olefin
With the monomer comprising polar substituent such as acrylate or acrylamide and poly- (ethylene oxide)-substitutional crylic acid
The copolymer of ester.The example of its polymeric dispersant is disclosed in following United States Patent (USP)：3,329,658、3449,250、3,519,
656th, 3,666,730,3,687,849 and 3,702,300.
Disclosure of the above-mentioned patent on ashless dispersant is incorporated herein by quoting.
Ashless dispersant is the important additives in engine lubricant for numerous purposes.Dispersant moistens in engine
One function in lubrication prescription is to maintain solid particle suspension, thus controls undesired engine deposits.However, dispersant exists
Handling rate in engine is higher, and dispersant may more cause engine sealing degraded and corrosion.Accordingly, it is desirable to provide enough
Polarity is to serve as dispersant, but the ashless compound for not causing sealing to degrade or corrode.
Summary of the invention
Inventor is generated with enough polarity to serve as the ashless compound of the non-alkaline of dispersant.
One aspect of the invention is related to ashless compound, and it includes long chain hydrocarbon groups, preferably long chain olefinic unsaturated alkyl, example
As polyolefin is for example poly- (isobutene) (" PIB "), the reaction with aldehyde such as formaldehyde either its derivative or reactive equivalent or ketone
Product.
In one embodiment, producing the reaction of reaction product may include that acid catalysis Alder-ene reactions or Prins are anti-
At least one of answer.
In one embodiment, ashless compound reaction product can be that alkyl substitutes cyclic ether compounds.Alkyl substitutes
Cyclic ether compounds can include by the ring group with 5 carbon atoms and 1 oxygen atom into cyclic ethers.Cyclic ethers can have 0 or 1 interior alkene
Belong to double bond.At least one in 5 carbon atoms of cyclic ethers can be by long chain hydrocarbon groups, such as polyolefin, including PIB substitutes.Equally, ring
One in 5 carbon atoms of ether can be substituted by the short-chain hydrocarbon group with 1 to about 10 carbon atom, or necessary amounts hydrogen with complete
Chemical valence at substitution carbon atom.It is preferred that long chain hydrocarbon groups, such as polyolefin/PIB are substituted by what is separated with the oxygen atom of cyclic ethers
At least one carbon atom on cyclic ethers.
In one embodiment, alkyl substitution cyclic ether compounds can be polyolefin substituted-dihydro pyrans.
In another embodiment, alkyl substitution cyclic ether compounds can be polyolefin substituted-tetrahydro pyrans.
In another embodiment, alkyl substitution cyclic ether compounds can include the compound of formula 1：
Wherein：
R、R1And R2It can be independently following at least one：(1) long chain hydrocarbon groups, or (2) H,
r1-r7It can be independently following at least one：(1) H, (2) short-chain hydrocarbon group, (3) by with by with from ring-type ether ring
Upper adjacent carbon atom " r " interaction formed interior olefinic double bond, and (4) be not present with contribute to by with phase on ring-type ether ring
" r " or " R " substituent with carbon atom interacts the outer olefinic double bond to be formed.
Alkyl substitution cyclic ether compounds an embodiment can be the compound of formula 1, wherein for 140 to about
5000Mn PIB, R1、R2And r1-r3In each, r6And r7For H, and r4And r5Olefinic double bond in interaction formation.
Surprisingly, alkyl substitution cyclic ether compounds described herein contribute to the cleaning for improving engine lubricant to inventor
Property.In addition, alkyl substitution cyclic ether compounds described herein do not influence engine sealing or cause to corrode.
Therefore, another aspect of the present invention is a kind of composition, the composition to include：(A) there is the oil of lubricant viscosity, and
(B) one in the embodiment above of alkyl substitution cyclic ether compounds.
In one embodiment, composition can optionally include (C) dispersant, and the dispersant includes carboxylic acid, amine, Manny
At least one of uncommon, post processing or polymeric dispersant.It is preferred that dispersant is carboxylic dispersants, most preferably PIB- succinyls are sub-
Amine.In one embodiment, composition can include the carboxylic dispersants based on the weight % of active material about 0.01 to about 20.
In yet another embodiment, the present invention relates to the method for operation engine, methods described to include：(1) to engine
Middle infeed composition, the composition, which includes (A), has the oil of lubricant viscosity, and (B) alkyl substitutes cyclic ethers as described herein
At least one of compound and optional (C) carboxylic acid, amine, Mannich, post processing or polymeric dispersant, and (2) operation engine.
Detailed description of the invention
Each preferred feature and embodiment are described below by non-limiting illustrate.
In one embodiment, the present invention relates to ashless compound, the ashless compound to include long chain hydrocarbon groups and aldehyde
Or the reaction product of ketone.
As used herein, term " hydrocarbyl substituent " or " alkyl " are made with its conventional meaning well known to those skilled in the art
With.Specifically, it refers to the group with the carbon atom being connected directly between on molecule remainder and mainly with hydrocarbon property.Hydrocarbon
The example of base includes：Hydrocarbon substituent, including aliphatic, alicyclic and aromatic substituent；Substituted hydrocarbon substituent, that is, contain in this hair
The substituent of the main hydrocarbon property of substituent or the non-hydrocarbon of its degree of functionality is not changed in bright context；With miscellaneous substituent, i.e.,
Similarly there is main hydrocarbon property but the substituent different from carbon is included in ring or chain.Term " hydrocarbyl substituent " or " alkyl "
Be defined in disclosed application US 2010-0197536 [0137]-[0141] section and find in more detail.
The long chain hydrocarbon groups of reaction product can include about 10 to about 600 carbon atoms, it is alternatively that about 25 to about 500 carbon originals
Son, or in another alternative, about 50 to about 400 carbon atoms, or about 50 to about 200 carbon atoms.It is preferred that long-chain
Alkyl can be linear or branched and is made up of carbon and hydrogen atom.
It is preferred that long chain hydrocarbon groups are ethylenically unsaturated hydrocarbons base.Alkyl can have high methylvinylidene isomer content.These
Including wherein at least about 50 weight %, in one embodiment, at least about 70 weight % alkyl have methyl ethenylidene end
The alkyl of base.
It is preferred that long chain hydrocarbon groups can be polyolefin.Polyolefin for preparing reaction product can be homopolymer, copolymer
Or interpretation.Polyolefin can be by comprising about 2 to about 16, the either polymerizable list of about 2 to about 8 or about 2 to about 6 carbon atoms
It is prepared by body.Generally, polymerisable monomer include ethene, propylene, isobutene, 1- butylene, isoprene, 1,3-butadiene, decene or
One or more in its mixture.
Polyolefin can be " routine " polyolefin or " high vinylidene " polyolefin and preferred " high vinylidene ".It is conventional
Difference between polyolefin and high vinylidene polyolefin can be illustrated by reference to the preparation of poly- (isobutene) (" PIB ").Making
In standby conventional PIB method (a), make isobutene in AlCl3In the presence of polymerization to produce mainly include three substituted olefines (III)
With four substituted olefines (IV) end group and only very low amount (such as less than 20%) chain includes the polymer of terminal vinylidene (I)
Mixture.In alternative (b), make isobutene in BF3It polymerize in the presence of catalyst to produce mainly (for example, at least
70%) mixture of the polymer comprising terminal vinylidene, less amount of four substitution end group and other structures.In alternative
The material of preparation, and sometimes referred to as " high vinylidene PIB ", is also described in United States Patent (USP) 6, and 165,235, in table 1.
The representative instance of polyolefin includes PIB；Polypropylene；Polyethylene；Copolymer derived from isobutene and butadiene；Spread out
It is born from the copolymer of isobutene and isoprene；Or its mixture.Useful polyolefin includes having 140-5000, in another feelings
400-2500 under condition, in still other cases 140 or 500 to 1500 number-average molecular weight PIB.PIB can have 5-69%,
50-69% in the case of two kinds, in a third case 50-95% ethenylidene double bond content.
In formation in the reaction product, the relative concentration of the reaction condition and this kind of component of long chain hydrocarbon groups and aldehydes or ketones
Should be preferably enough so that most of long chain hydrocarbon groups are reacted with least one aldehydes or ketones molecule.That is, for the optimal of dispersant
Performance, preferably no more than 30 weight % polyisobutene or other long chain hydrocarbon groups should keep unreacted in gained dispersant.It is preferred that
It should keep not more than 25% unreacted long chain hydrocarbon groups, more preferably no more than 20%.Ensure the measure of the condition of enough extents of reaction
In the ability of those skilled in the art.
Aldehydes or ketones reactant for preparing reaction product is the carbonyls different from carboxyl substituted carbonyl compound
(i.e. non-carboxyl substituted carbonyl compound).Suitable compound includes those with general formula R C (O) R', and wherein R and R' are each
It independently is H or there is about 1 to about 10, the alkyl of preferably 2 to about 4 carbon atoms.As noted in the discussion, alkyl can wrap
Containing the other groups or hetero atom for not disturbing the inventive method and product.It is preferred that aldehydes or ketones include 1 to about 12 carbon atom.
Aldehyde for forming reaction product can have 1-10, either 1-8 or 1-6 carbon atom.Suitable aldehyde includes first
Aldehyde, acetaldehyde, propionic aldehyde, butyraldehyde, isobutylaldehyde, valeral, hexanal, enanthaldehyde, octanal, benzaldehyde and more advanced aldehyde.Usual other aldehyde, such as
Dialdehyde, especially glyoxal are useful, but generally preferably single aldehyde.In one embodiment, non-carboxyl substituted carbonyl chemical combination
Thing is that alkyl substitutes aldehyde, and preferably alkyl substitutes single aldehyde.
Most preferred aldehyde is formaldehyde, and it can be provided as the aqueous solution of commonly referred to as formalin, but more generally as oligomeric
Formaldehyde is used with polymer form, its reactive equivalent or source for formaldehyde.Other reactive equivalents include hydrate
Or cyclic trimer.In one embodiment, it is made up of for forming the aldehyde of reaction product single aldehyde such as formaldehyde.
Suitable ketone includes acetone, butanone, MEK and other ketone.It is preferred that one kind in alkyl is methyl.
The mixture of two or more aldehyde and/or ketone is also useful.In one embodiment, react by long chain hydrocarbons
Base such as PIB, and aldehyde, preferably single aldehydes or ketones composition.
The reaction prepared in reaction product is related to one or more equivalent acid additions by aldehydes or ketones on polyolefin.Instead
It is able to should be reacted by two kinds of neighbouring Alder-ene, the closed loop of acid regulation and control thereafter, or Prins chemistry are carried out.In an embodiment party
In case, reaction (such as Alder-ene or Prins reactions) can be carried out in the absence of underwater.In another embodiment, reaction can
Carried out in dry conditions using solid aldehyde such as solid formaldehyde (i.e. paraformaldehyde).
In one embodiment, reaction product includes alkyl substitution cyclic ether compounds.Alkyl substitution cyclic ether compounds can
Comprising by the ring group with 5 carbon atoms and 1 oxygen atom into cyclic ethers.The ring of cyclic ethers can include 0 interior olefinic double bond, or
1 interior olefinic double bond.In addition, at least one in 5 carbon atoms of ring-type ether ring can be substituted by following group：(1) long chain hydrocarbons
Base, such as polyolefin as described above, (2) short-chain hydrocarbon group, or (3) completion substitute the hydrogen of the required number of the chemical valence on carbon.
Long chain hydrocarbon groups can be polyolefin as described above.When ring-type ether ring by long chain hydrocarbon groups for example polyolefin substitutes when, long-chain
Alkyl is incorporated on carbon atom, and wherein at least one carbon atom separates with the oxygen atom of ring-type ether ring.
Short-chain hydrocarbon group may be incorporated in any one in 5 carbon atoms of ring-type ether ring on.Short-chain hydrocarbon group preferably comprises 1 to about
10 carbon atoms, it is alternatively that 1 to about 8 carbon atom, or alternately, 1 to about 6 carbon atom.Short-chain hydrocarbon group is excellent
Elect as linear or branched, but can also include aryl.It is preferred that short-chain hydrocarbon group is made up of carbon and hydrogen atom, but it can also include it is miscellaneous
Atom, such as nitrogen, oxygen and sulphur.Hetero atom can especially exist as a part for heteroaryl.Short-chain hydrocarbon group can be hydrogenation, example
Such as methyl, or olefinic double bond can be included, such as methylene.
It is well known to those skilled in the art to complete the hydrogen of the required number of chemical valence on carbon atom, wherein considering that hydrocarbon substitutes
Base and any interior olefinic double bond related to the specific carbon atom.
In one embodiment, alkyl substitution cyclic ether compounds can be illustrated by the compound of formula 1：
Wherein：
R、R1And R2It can be independently following at least one：(1) long chain hydrocarbon groups as defined above, preferably as above
Defined polyolefin, most preferably as hereinbefore defined and there is 140-5000, in another case 400-2500, in another feelings
The PIB of 140 or 500 to 1500 number-average molecular weight under condition, or (2) H,
r1-r7It can be independently following at least one：(1) H, (2) short-chain hydrocarbon group as defined above, (3) by from
The r of adjacent carbon atom reacts to each other the interior olefinic double bond to be formed on ring-type ether ring, and (4) be not present with contribute to by with identical ring
The r or R substituent of shape ether ring carbon atom interact the outer olefinic double bond to be formed.
In a preferred embodiment, formula 1 can be the polyolefin substituted-dihydro pyrans for example represented by formula 1 (a), its
Middle R is or PIB, R more particularly as defined above to about 5000Mn with 1401、R2And r1-r3In each,
r6And r7For H, and r4And r5Olefinic double bond in interaction formation.
In another preferred embodiment of the present, formula 1 can be the polyolefin substituted-tetrahydro pyrans for example represented by formula 1 (b), its
Middle R is or PIB more particularly as defined above, wherein r to about 5000Mn with 1404Outside double bond is contributed to, and
R1、R2And r1-r3And r5-r7Respectively H.
In another optional embodiment, formula 1 can be the polyolefin substituted-tetrahydro pyrans for example represented by formula 1 (c), its
Middle R1For with 140 to about 5000Mn, or PIB, R and r more particularly as defined above4Interaction, which is formed, has 1
Carbon atom and the short-chain hydrocarbon group with olefinic double bond, i.e. methylene, and R2、r1-r3And r5-r7Respectively H.
One aspect of the present invention is engine lubricant, and it, which includes (A), has the oil of lubricant viscosity, and (B) ashless compound,
I.e. above-mentioned alkyl substitution cyclic ether compounds.
In one embodiment, (B) ashless compound described herein can using based on active material as lubricating composition
0.01 weight % to 20 weight %, either 0.05 weight % to 10 weight % or 0.08 weight % be to 5 weight %, or
0.1 weight % to 3 weight % scope is added in the oil that (A) has lubricant viscosity.
(A) oil with lubricant viscosity may include for example natural and artificial oil, derived from being hydrocracked, hydrogenate and be hydrogenated with essence
The oil of system, do not refine, refine and refined oil and its mixture again.Oil with lubricant viscosity also can be such as American
Definition described in Petroleum Institute (API) Base Oil Interchangeability Guidelines.
The various oily more comprehensively detailed descriptions that can be used in the present invention can disclosed in 15 days December in 2011 Gieselman etc.
Found in the U.S. Publication #2011/0306528 of people [0104]-[0111] section.
Lubricant compositions can be concentrate and/or prepare the form of lubricant completely.If ashless dispersants of the present invention
Agent is the form (it can be combined completely or partially to form final lubricant with other oil) of concentrate, then ashless dispersant
Include 1 with the oil with lubricant viscosity and/or with the ratio of flux oil:99-99:1 weight meter, or 80:20-10:90 weight meters
Scope.
Composition can optionally include (C) dispersant, and the dispersant includes carboxylic acid, amine, Mannich, post processing and polymerization point
At least one of powder.
Dispersant is commonly referred to as ashless dispersant, because before being mixed into lubricant oil composite, they do not include into ash
Metal, and they add lubricant with polymeric dispersant before generally do not contribute any into grey metal.Ashless type dispersants
It is characterized in the polar group being connected on higher molecular weight hydrocarbon chain.Typical ashless dispersant includes carboxylic dispersants, such as
The long chain alkene base succinimide of N- substitutions.The example of the long chain alkene base succinimide of N- substitutions includes PIB substituents
Number-average molecular weight be 350-5000, or 500-3000 PIB succinimides.Succinimide dispersants and its preparation are public
Open in such as United States Patent (USP) 4,234,435.Succinimide dispersants are usually usual poly- (vinylamine) or aromatics by polyamines
The acid imide that polyamines such as aminodiphenylamine (ADPA) is formed.
In one embodiment, lubricant compositions can further include amine dispersant, for example, PIB succinic anhydrides and
Amine, preferably polyamines, preferred aliphatic series polyamines, such as ethylene (i.e. poly- (vinylamine)), propylidene polyamines, butylidene polyamines or
The reaction product of its mixture of two or more of person.Aliphatic polyamines can be ethylene.Aliphatic polyamines may be selected from second
Diamines, diethylenetriamines, trien, tetren, penten, polyamines kettle it is residual or its two kinds or
More kinds of mixtures.
In one embodiment, lubricant compositions are further 350- derived from number-average molecular weight comprising at least one
5000 or 500-3000 PIB PIB succinimide dispersants.PIB succinimides can individually or with other dispersant groups
Close and use.
Another kind of ashless dispersant is Mannich base.Mannich dispersant is alkylphenol and aldehyde (especially formaldehyde) and amine
The reaction product of (especially polyalkylene polyamine).Alkyl generally comprises at least 30 carbon atoms.
Also can by dispersant by conventional method by being post-processed with the reaction of any of plurality of reagents.Wherein, this
It is a little for boron, urea, thiocarbamide, dimercaptothiodiazole, carbon disulfide, aldehyde, ketone, carboxylic acid, the succinic anhydrides of hydrocarbon substitution, maleic anhydride, nitrile,
Epoxides, phosphorus compound and/or metallic compound.
Optional dispersant can also be polymeric dispersant.Polymeric dispersant be oil-soluble monomer such as decyl-octyl methacrylate,
Vinyl decyl ether and high molecular weight olefin, with the monomer comprising polar substituent such as acrylate or acrylamide
With the copolymer of poly- (ethylene oxide)-substituted acrylate.
(C) optionally dispersant can be with 0 weight % of lubricating composition to 20 weight %, or 0.1 weight % to 15 weights
% is measured, either 0.1 weight % to 10 weight % or 1 weight % to 6 weight %, or 3 weight % to 12 weight % are present.
Engine lubricant can also include conventional detersive (being prepared by method as known in the art).Engine lubrication
The most frequently used detersive (is typically based on the metal hydrogen-oxygen of metal such as calcium, magnesium, zinc or sodium due to alkaline metal-containing compound in field
Compound, oxide or carbonate) presence and obtain its most or all basicity.Also referred to as parlkaline or hyperalkaline salt is this kind of
Metal overbased detergent is usually single-phase homogeneous Newtonian systems, it is characterized in that tenor exceedes according to metal and and metal
In the stoichiometry of the specific acidic organic compound of reaction and existing for meeting.Parlkaline material is generally (logical by acid material
Normal inorganic acid or lower level carboxylic acid such as carbon dioxide) and acidic organic compound (also referred to as matrix), the gold of stoichiometric excess
Belong to the mixture of alkali, generally in inert organic solvents (such as mineral oil, naphtha, toluene, two for acid organic media
Toluene) reaction medium in react and prepare.A small amount of accelerator such as phenol or alcohol are there is typically further, and it is few in some cases
Measure water.The acid organic substrate generally carbon atom with enough numbers is to provide the solubility in oil.
Parlkaline may be selected from without thiophenol salt, sulfur-bearing phenates, sulfonate, salixarate, salicylic acid containing metal detergent
Salt and its mixture, or its boration equivalent.Overbased detergent boric acid agent such as Boric acid boron can be acidified.
Overbased detergent is as known in the art.In one embodiment, sulfonate detergent can be with
At least 8 metal than dominant linear alkylbenzenesulfonate detersive, such as the of U.S. Patent application 2005-065045
[0026]-[0037] described in section.Term " metal ratio " is the total yield of metal and the ratio between the equivalent of acidic organic compound.In
Property metal salt have 1 metal ratio.With with gold of the salt of 4.5 times of metals as many with 3.5 equivalents present in normal salt
Category is excessive, or 4.5 ratio.
In one embodiment, parlkaline is calcium or magnesium overbased detergent containing metal detergent.In an embodiment party
In case, lubricating composition includes overbased calcium sulfonate, parlkaline calcium phenoxide or its mixture.Overbased detergent, which can include, to be had
At least 3 metal than sulfoacid calcium.
Overbased detergent of the present invention can exist with 0.05 weight % of composition to 5 weight % amount.In other realities
Apply in scheme, overbased detergent can be with the weight of the 0.1% of lubricating composition, 0.3% or 0.5% to 3.2%, 1.7% or 0.9
% is measured to exist.Similarly, overbased detergent can be suitable for being supplied to lubricating composition 1TBN to 10TBN amount to exist.
In other embodiments, overbased detergent is to be supplied to lubricating composition 1.5TBN or 2TBN to 3TBN, 5TBN or 7TBN
Amount is present.
Engine lubricant can also include other performance additive.Other performance additive can include metal deactivator, glue
Spend modifier, friction improver, antiwear additive, corrosion inhibitor, dispersant viscosity modifiers, extreme pressure agent, anti-scratch liniment, anti-oxidant
Agent, foam inhibitor, demulsifying agent, pour-point depressant, sealing at least one of sweller and its mixture.Generally, prepare completely
Lubricating oil includes the one or more in these performance additives.
In one embodiment, it is existing optionally performance additive total combined amount can be lubricating composition 0 or
0.01 weight % to 50 weight %, in another embodiment, 0 or 0.01 to 40 weight %, in another embodiment, 0 or
0.01 to 30 weight %, in another embodiment, 0.05 or 0.1 or 0.5 to 20 weight %.In one embodiment, deposit
Other performance additive compound total combined amount based on oil-free for composition 0 weight % to 25 weight % or 0.01 weight
Measure % to 20 weight %.Although one or more other performance additives may be present, usual other performance additive is not with each other
Same amount is present.
Lubricating composition can be used in internal combustion engine.Internal combustion engine can be with or without scheme for exhaust gas circulation system.
In one embodiment, internal combustion engine can be diesel combustion engine (usual large diesel engine), gasoline combustion
Engine, combustion of natural gas engine or blend gasoline/alcohol combustion engine.In one embodiment, internal combustion engine can be
Diesel combustion engine, it is in another embodiment gasoline combustion engine.In one embodiment, engine can be
Spark ignition engine, it is compression engine in one embodiment.
Internal combustion engine can be 2 strokes or 4 Stroke Engines.Suitable internal combustion engine includes marine diesel, aviation piston
Formula engine, low load diesel engine and automobile and truck engine.
Lubricant compositions for internal combustion engine may be adapted to any engine lubricant but regardless of sulphur, phosphorus or sulfate ash
(ASTM D-874) content.The sulfur content of engine oil lubricants can be 1 weight % or less, or 0.8 weight % or more
Lack, either 0.5 weight % or less or 0.3 weight % or less.In one embodiment, sulfur content can be 0.001
Weight % to 0.5 weight %, or 0.01 weight % to 0.3 weight %.Phosphorus content can be 0.2 weight % or less, or
0.1 weight % or less, either 0.085 weight % or less or even 0.06 weight % or less, 0.055 weight % or
Less, or 0.05 weight % or less.In one embodiment, phosphorus content can be 100ppm to 1000ppm, or
325ppm to 700ppm.Total sulfate ash content can be 2 weight % or less, either 1.5 weight % or less or 1.1
Weight % or less, either 1 weight % or less or 0.8 weight % or less, or 0.5 weight % or less.At one
In embodiment, sulfate ash content can be 0.05 weight % to 0.9 weight %, or 0.1 weight % to 0.2 weight % is extremely
0.45 weight %.
In one embodiment, lubricating composition is engine oil, and wherein lubricating composition is characterized in as follows
At least one of：(i) 0.5 weight % or less sulfur content, (ii) 0.1 weight % or less phosphorus content, and (iii) 1.5
Weight % or less sulfate ash content.
In one embodiment, lubricating composition includes and is less than 1.5 weight %, either less than 1.25% or is less than
1.0% unreacted polyisobutene.
Ashless dispersants immunomodulator compounds and lubricating composition comprising ashless dispersants immunomodulator compounds can be by by ashless compounds
Or the lubricating composition comprising ashless compound feeds in engine and operates engine and be used to improve the deposition in engine
In the method for one in physical performance, sealing property and corrosive nature.
In one embodiment, ashless dispersants immunomodulator compounds do not contribute to total acid number (TAN) or total base number (TBN), i.e.,
The TAN and TBN of compound (mean that only trace is for example relevant with impurity, but not effectively assign and matching somebody with somebody substantially for 0 or essentially 0
Preparation TAN or TBN).In another embodiment, TAN be less than about 5, either in some embodiments 4 or even 3 or
2, preferably less than 1.In another embodiment, TBN be less than about 5, or in embodiments below, 4 or even 3 or
2, preferably smaller than 1.
The PIB succinimides of additional amount, such as PIB succinic anhydrides and amine, preferred aliphatic series amine, preferred aliphatic series polyamines is as gathered
The reaction product of ethylene (PEPA) can be used in this method.
Unless otherwise indicated, the amount of each chemical constituent is expressed as eliminating and generally may be present in commercial materials
Any solvent or flux oil, i.e., based on active chemical.However, unless otherwise indicated, each chemicals or group being mentioned above
Compound should be understood to containing isomers, accessory substance, derivative and generally it should be understood that be present in commerical grade it is other this
The commercial grade material of class material.
Some known above-mentioned materials may interaction in final preparaton so that the component of final preparaton may be with
Originally those added are different.For example, metal ion (such as detersive) it can migrate to the other acid or cloudy of other molecules
Ion position.The product being consequently formed, including the product through being formed with its intended use using the present composition may not
Easily description.However, all such improvement and reaction product are included within the scope of the present invention；The present invention will be upper including passing through
The composition stated component mixing and prepared.
As used herein, transition phrase "comprising", " substantially by ... form " and " Consists of " definition if any, are closed
Do not include the scope of the disclosure of other components or step not described in the scope of disclosed embodiment.With " bag
Include ", " containing " or " being characterized in ... " synonymous transitional term "comprising" be inclusive or open, and be not excluded for other not retouching
The element or method and step stated.On the contrary, transition phrase " Consists of " is not any including not described in disclosed embodiment
Element, step or composition.Transition phrase " substantially by ... form " is intended to make the scope of disclosed embodiment to be limited to the material
Or step, and technical staff should be understood the basic and new feature of embodiment disclosed in not substantial effect those materials or
Step.Term " Consists of " and " substantially by ... form " can be used as optional embodiment for instead of in disclosure above
"comprising" sentence.
Embodiment
Sample 1：The reaction product of long chain hydrocarbon groups and aldehyde
Thermocouple, inputting type agitator, nitrogen cleaning, heating mantles and the addition leakage of solid screw thread will be assembled in 1L four-neck flasks
Bucket.445g 1000Mn high vinylidenes PIB is fitted into flask and cleans assembling with nitrogen (0.5scfh).Add methane
Sulfonic acid (0.6g) and as stirring heats the mixture to 115 DEG C.By addition funnel the oligomeric first of 30.1g was added through 3.5 hours
Aldehyde.Temperature is improved to 120 DEG C, and preparation is stirred 4 hours.Preparation is cooled to 90 DEG C and adds sodium hydroxide (in water
50%, 0.5g).Temperature is improved to 130 DEG C and stirred 1 hour.Flask is cooled to 90 DEG C and adds diatomite.By product mistake
Filter to obtain 380g.
Embodiment 1：
Sample 1 is provided in following table relative to 1550Mn succinimide dispersants (succinimide) and 1000Mn PIB
The contrast of total acid number (TAN), total base number (TBN) and retention factors (Rf values, the measurement of polarity).
The dispersant of table 1. contrasts
Embodiment 2：
4 kinds of mid-SAPS oil (the sulfate ash limit 0.8%) preparatons are prepared, it includes succinimide and with 3%w/w
Push up the combination of the sample 1 of processing.Also preparing only has the control formulation of succinimide.According to Volkswagen VitonTM
Leakage test PV-3344 tests preparaton.PV-3344 experiments are designed for assessing engine oil to Parker-Pradifa
The Industry Standard Test of the influence of SRA AK6 (fluorine carbon) encapsulant.Measure the tensile strength of sample, elongation at break and split
Change.Preparaton (w/w yls) and sealing result (final tensile strength and final fracture elongation intensity) are shown in table 2.It is higher
Value represent preferable sealing property.
Table 2. contrasts and preparaton of the present invention
Table 2 shows that when standard succinimide dispersants are reduced sealing property is improved.The data are also shown comprising this hair
Bright dispersant does not interfere with the final tensile strength of sealing, actually improves elongation at break.
Embodiment 3：
Use VolkswagenTM1.6L Diesel Intercooler test (VolkswagenTMVW TDI are tested) survey
Trial preparation 1 is relative to control formulation.TDI engine tests are that the turbo-charged direct injection of 54 hours is run under specified requirements
Igniter motor is tested.In off-test, with the cleannes of 0-100 grade visual evaluation piston, wherein 100 represent piston
It is clean and be free of deposit.Table 3 shows all parts on piston, including groove 1-3 and the first and second platforms
(land) grade point.
Table 3. contrasts and the VW TDi performances of lubricant of the present invention
Obvious groove 2 is greatly improved due to the presence of inventive dispersant in sample 1, and platform 2 also directionally changes
Enter.
Most important grade point is weighted average piston grade point.The presence of inventive dispersant makes average etc. in sample 1
Level value improves almost 9 units.This is considered as the big improvement in the experiment and is directly attributed to the presence of sample 1.
Above-mentioned each file is incorporated by reference into the present invention.Any file refer to be not allow this document with
Any authority obtains the qualification of prior art or forms the general knowledge of technical staff.Except embodiment China and foreign countries, or if clearly refer in addition
Go out, all quantity of the amount of material, reaction condition, molecular weight, carbon number etc. should be understood to pass through described in the specification
Wording " about " is modified.It should be understood that the upper and lower bound of amount described herein, scope and ratio can be combined independently.Similarly, this hair
The scope and amount of bright each element can be used together with the scope or amount of any other element.As used herein, statement is " basic
By ... form " allow to include not influence the considered essential characteristic of composition and the material of new feature substantially.
Claims (14)
1. ashless compound, it includes long chain olefinic unsaturated alkyl and the non-carboxyl substituted carbonyl compound selected from aldehyde and ketone
Reaction product, wherein compound are polyolefin substituted-dihydro pyrans.
2. compound according to claim 1, wherein the long chain olefinic unsaturated alkyl includes 10 to 600 carbon atoms.
3. according to the compound of claim 1 or 2, wherein the long chain olefinic unsaturated alkyl is that the number with 140-5000 is equal
The polyolefin of molecular weight.
4. according to the compound of claim 1 or 2, wherein the non-carboxyl substituted carbonyl compound, which is alkyl, substitutes single aldehyde.
5. according to the compound of claim 1 or 2, wherein the aldehyde is formaldehyde or its derivative or reactive equivalent.
6. according to the compound of claim 1 or 2, wherein the reaction includes acid catalysis Alder-ene reactions or Prins reactions
At least one of.
7. compound according to claim 6, wherein the reaction is carried out in the absence of underwater.
8. compound according to claim 3, wherein polyolefin are the PIB with 140 to 5000 number-average molecular weight.
9. a kind of composition, it is included：(A) there is the oil of lubricant viscosity, and (B) ashless compound, it includes long chain olefinic not
Saturated hydrocarbyl and the reaction product selected from aldehyde and the non-carboxyl substituted carbonyl compound of ketone, wherein compound are polyolefin substitution two
Hydrogen pyrans.
10. composition according to claim 9, it also includes (C) dispersant, and the dispersant includes carboxylic dispersants, amine point
Powder, Mannich dispersant, post processing at least one of dispersant or polymeric dispersant.
11. composition according to claim 10, wherein dispersant are carboxylic dispersants.
12. composition according to claim 11, wherein the carboxylic dispersants are PIB- succinimides.
13. composition according to claim 11, the carboxylic dispersants are with based on the weight of active material 0.01 to 20 % presence.
14. operating the method for engine, it includes：(1) composition is fed into engine, it is included：(A) there is lubricant viscosity
Oil, and (B) ashless compound, it includes long chain olefinic unsaturated alkyl and non-carboxyl substituted carbonyl chemical combination selected from aldehyde and ketone
The reaction product of thing, wherein compound are polyolefin substituted-dihydro pyrans, and (2) operation engine.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261734431P | 2012-12-07 | 2012-12-07 | |
| US61/734,431 | 2012-12-07 | ||
| PCT/US2013/071121 WO2014088814A1 (en) | 2012-12-07 | 2013-11-21 | Pyran dispersants |
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| CN104955928A CN104955928A (en) | 2015-09-30 |
| CN104955928B true CN104955928B (en) | 2018-02-09 |
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| CN201380071774.7A Active CN104955928B (en) | 2012-12-07 | 2013-11-21 | Pyrans dispersant |
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| US (1) | US9695377B2 (en) |
| EP (1) | EP2928994B1 (en) |
| KR (1) | KR102125974B1 (en) |
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| EP3186343B1 (en) * | 2014-08-28 | 2019-10-09 | The Lubrizol Corporation | Lubricating composition with seals compatibility |
| JP6867622B2 (en) * | 2016-07-29 | 2021-04-28 | 山本香料株式会社 | Odor modulation oil and lubricating oil |
| JP6853524B2 (en) * | 2016-07-29 | 2021-03-31 | 山本香料株式会社 | Odor modulation method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248327A (en) * | 1963-10-02 | 1966-04-26 | Gulf Research Development Co | Lubricating composition |
| CN101180284A (en) * | 2005-05-25 | 2008-05-14 | 默克专利股份有限公司 | Method for producing tetrahydropyranes from tetrahydropyran-3-ones |
| CN101679898A (en) * | 2007-06-11 | 2010-03-24 | 出光兴产株式会社 | Detergent dispersant, additive composition for lubricant, and lubricating oil composition |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE672370C (en) * | 1932-11-27 | 1939-02-28 | I G Farbenindustrie Akt Ges | Process for the preparation of condensation products containing sulfuric acid residues |
| US2362307A (en) * | 1940-05-11 | 1944-11-07 | Standard Oil Dev Co | Cyclic diethers |
| US2452977A (en) * | 1944-12-28 | 1948-11-02 | Shell Dev | Production of cyclic ethers |
| US3036003A (en) | 1957-08-07 | 1962-05-22 | Sinclair Research Inc | Lubricating oil composition |
| DE1248643B (en) | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Process for the preparation of oil-soluble aylated amines |
| US3444170A (en) | 1959-03-30 | 1969-05-13 | Lubrizol Corp | Process which comprises reacting a carboxylic intermediate with an amine |
| NL121826C (en) | 1959-07-24 | |||
| US3236770A (en) | 1960-09-28 | 1966-02-22 | Sinclair Research Inc | Transaxle lubricant |
| US3200107A (en) | 1961-06-12 | 1965-08-10 | Lubrizol Corp | Process for preparing acylated amine-cs2 compositions and products |
| US3449250A (en) | 1962-05-14 | 1969-06-10 | Monsanto Co | Dispersency oil additives |
| US3329658A (en) | 1962-05-14 | 1967-07-04 | Monsanto Co | Dispersency oil additives |
| DE1271877B (en) | 1963-04-23 | 1968-07-04 | Lubrizol Corp | Lubricating oil |
| US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
| US3282955A (en) | 1963-04-29 | 1966-11-01 | Lubrizol Corp | Reaction products of acylated nitrogen intermediates and a boron compound |
| US3513093A (en) | 1963-06-17 | 1970-05-19 | Lubrizol Corp | Lubricant containing nitrogen-containing and phosphorus-containing succinic derivatives |
| NL137371C (en) | 1963-08-02 | |||
| US3455832A (en) | 1963-09-09 | 1969-07-15 | Monsanto Co | Schiff bases |
| GB1053577A (en) | 1963-11-01 | |||
| USRE26433E (en) | 1963-12-11 | 1968-08-06 | Amide and imide derivatives of metal salts of substituted succinic acids | |
| GB1052380A (en) | 1964-09-08 | |||
| US3316177A (en) | 1964-12-07 | 1967-04-25 | Lubrizol Corp | Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene |
| NL145565B (en) | 1965-01-28 | 1975-04-15 | Shell Int Research | PROCESS FOR PREPARING A LUBRICANT COMPOSITION. |
| US3414347A (en) | 1965-03-30 | 1968-12-03 | Edroy Products Company Inc | Binocular with pivoted lens plate |
| DE1595234A1 (en) | 1965-04-27 | 1970-03-05 | Roehm & Haas Gmbh | Process for the preparation of oligomeric or polymeric amines |
| US3340281A (en) | 1965-06-14 | 1967-09-05 | Standard Oil Co | Method for producing lubricating oil additives |
| US3574576A (en) | 1965-08-23 | 1971-04-13 | Chevron Res | Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine |
| US3539633A (en) | 1965-10-22 | 1970-11-10 | Standard Oil Co | Di-hydroxybenzyl polyamines |
| US3442808A (en) | 1966-11-01 | 1969-05-06 | Standard Oil Co | Lubricating oil additives |
| US3433744A (en) | 1966-11-03 | 1969-03-18 | Lubrizol Corp | Reaction product of phosphosulfurized hydrocarbon and alkylene polycarboxylic acid or acid derivatives and lubricating oil containing the same |
| US3461172A (en) | 1966-11-22 | 1969-08-12 | Consolidation Coal Co | Hydrogenation of ortho-phenolic mannich bases |
| US3702757A (en) | 1967-03-09 | 1972-11-14 | Chevron Res | Phosphate ester amine salts useful as fuel detergents and anti-icing agents |
| US3448047A (en) | 1967-04-05 | 1969-06-03 | Standard Oil Co | Lube oil dispersants |
| US3501405A (en) | 1967-08-11 | 1970-03-17 | Rohm & Haas | Lubricating and fuel compositions comprising copolymers of n-substituted formamide-containing unsaturated esters |
| US3519565A (en) | 1967-09-19 | 1970-07-07 | Lubrizol Corp | Oil-soluble interpolymers of n-vinylthiopyrrolidones |
| US3600372A (en) | 1968-06-04 | 1971-08-17 | Standard Oil Co | Carbon disulfide treated mannich condensation products |
| GB1244435A (en) | 1968-06-18 | 1971-09-02 | Lubrizol Corp | Oil-soluble graft polymers derived from degraded ethylene-propylene interpolymers |
| US3586629A (en) | 1968-09-16 | 1971-06-22 | Mobil Oil Corp | Metal salts as lubricant additives |
| US3725480A (en) | 1968-11-08 | 1973-04-03 | Standard Oil Co | Ashless oil additives |
| US3634515A (en) | 1968-11-08 | 1972-01-11 | Standard Oil Co | Alkylene polyamide formaldehyde |
| US3591598A (en) | 1968-11-08 | 1971-07-06 | Standard Oil Co | Certain condensation products derived from mannich bases |
| US3726882A (en) | 1968-11-08 | 1973-04-10 | Standard Oil Co | Ashless oil additives |
| US3702300A (en) | 1968-12-20 | 1972-11-07 | Lubrizol Corp | Lubricant containing nitrogen-containing ester |
| US3576743A (en) | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
| FR2042558B1 (en) | 1969-05-12 | 1975-01-10 | Lubrizol Corp | |
| US3632511A (en) | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
| US3639242A (en) | 1969-12-29 | 1972-02-01 | Lubrizol Corp | Lubricating oil or fuel containing sludge-dispersing additive |
| US3649659A (en) | 1970-03-24 | 1972-03-14 | Mobil Oil Corp | Coordinated complexes of mannich bases |
| US3708422A (en) | 1971-01-29 | 1973-01-02 | Cities Service Oil Co | Electric discharge machining fluid |
| US3897456A (en) * | 1973-02-16 | 1975-07-29 | Exxon Research Engineering Co | Sludge inhibitor for hydrocarbon oils |
| US3846319A (en) * | 1973-03-27 | 1974-11-05 | Chevron Res | Dioxan-containing aluminum lubricant |
| US3980569A (en) | 1974-03-15 | 1976-09-14 | The Lubrizol Corporation | Dispersants and process for their preparation |
| US4234435A (en) | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
| US6165235A (en) | 1997-08-26 | 2000-12-26 | The Lubrizol Corporation | Low chlorine content compositions for use in lubricants and fuels |
| US6482243B2 (en) | 2001-03-22 | 2002-11-19 | J.T. Granatelli Lubricants, Inc. | Fuel reformulator |
| DE60203639T2 (en) | 2001-11-05 | 2006-01-19 | The Lubrizol Corp., Wickliffe | Lubricant composition with improved fuel economy |
| FR2873922B1 (en) | 2004-08-06 | 2008-10-17 | Mane Fils Sa V | BETA-SUBSTITUTED TETRAHYDROPYRAN (ON), PROCESS FOR THEIR SYNTHESIS AND THEIR USE IN PERFUMERY |
| CA2688098C (en) | 2007-05-24 | 2016-04-19 | The Lubrizol Corporation | Lubricating composition containing ashfree antiwear agent based on hydroxypolycarboxylic acid derivative and a molybdenum compound |
| EP2050743A1 (en) * | 2007-10-19 | 2009-04-22 | Humboldt-Universität zu Berlin | Method for the synthesis of dl.(alpha)-tocopherol and means therefore |
| BRPI0920904B1 (en) | 2008-11-26 | 2020-01-07 | The Lubrizol Corporation | LUBRICATING COMPOSITION CONTAINING A POLYMER FUNCTIONED WITH A CARBOXYLIC ACID AND AN AROMATIC POLYAMINE |
-
2013
- 2013-11-21 CN CN201380071774.7A patent/CN104955928B/en active Active
- 2013-11-21 WO PCT/US2013/071121 patent/WO2014088814A1/en active Application Filing
- 2013-11-21 KR KR1020157017057A patent/KR102125974B1/en active IP Right Grant
- 2013-11-21 CA CA2893840A patent/CA2893840A1/en not_active Abandoned
- 2013-11-21 US US14/648,105 patent/US9695377B2/en active Active
- 2013-11-21 EP EP13808303.5A patent/EP2928994B1/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248327A (en) * | 1963-10-02 | 1966-04-26 | Gulf Research Development Co | Lubricating composition |
| CN101180284A (en) * | 2005-05-25 | 2008-05-14 | 默克专利股份有限公司 | Method for producing tetrahydropyranes from tetrahydropyran-3-ones |
| CN101679898A (en) * | 2007-06-11 | 2010-03-24 | 出光兴产株式会社 | Detergent dispersant, additive composition for lubricant, and lubricating oil composition |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014088814A1 (en) | 2014-06-12 |
| KR102125974B1 (en) | 2020-06-24 |
| CA2893840A1 (en) | 2014-06-12 |
| EP2928994A1 (en) | 2015-10-14 |
| KR20150093180A (en) | 2015-08-17 |
| US9695377B2 (en) | 2017-07-04 |
| CN104955928A (en) | 2015-09-30 |
| EP2928994B1 (en) | 2021-04-21 |
| US20150307804A1 (en) | 2015-10-29 |
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